CN109942519A - A method of 5- alkoxymethylfurfural is prepared using glucide - Google Patents
A method of 5- alkoxymethylfurfural is prepared using glucide Download PDFInfo
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Abstract
The invention belongs to organic solid castoff recycling fields, disclose a kind of method for preparing 5- alkoxymethylfurfural using glucide, characterized by the following steps: using the ionic liquid for containing bromide ion or the eutectic solvent for containing bromide ion as reaction phase, two-phase system is mutually constructed using organic solvent as extraction as reaction medium；Solid acid catalyst, glucide raw material, alcohols material raw material, reaction medium with strong lewis acid are added in reactor, glucide raw material is continuously converted into 5- alkoxymethylfurfural under the conditions of heating and stirring.The present invention can reduce the side reaction of bronsted acid catalysis, to greatly improve reaction efficiency and selectivity, improve transformation efficiency, green and economy that glucide is converted into 5- alkoxymethylfurfural class A fuel A additive, using liquid fuel etc. as extract mutually can reduce it is subsequent isolate and purify process, product is integrated directly into liquid fuel product.
Description
Technical field
The invention belongs to organic solid castoff recycling fields, prepare 5- alkane using glucide more particularly to a kind of
The method of oxygroup methyl furfural.
Background technique
Currently, China is very low to the utilization rate of the biomass resources such as agricultural crop straw, every year because crop straw burning, landfill are made
At economic loss and environmental pollution can not underestimate.It is produced and is cleaned as base stock using reproducible lignocellulose-like biomass
The energy, chemicals and material substitution petroleum chemicals are the effective ways alleviating energy resource crisis and curbing environmental pollution.It is domestic
The verified potentiality that petroleum refining is substituted by biorefinery of outer research work.By the highest carbohydrate object of content in biomass
Matter is converted into 5- ethoxyl methyl furfural via platform chemicals 5 hydroxymethyl furfural, is very representative and application prospect
Conversion pathway.(calorific value of 8.7 kWh/L, gasoline, diesel oil and ethyl alcohol is respectively 5- ethoxyl methyl furfural calorific value with higher
8.8,9.7 and 6.1 kWh/L), it is expected to the liquid fuel additive as a kind of green high-efficient, realizes that extensive industrialization is answered
With.It no matter is 5- ethoxyl methyl furfural for academic research or practical application by the glucide Efficient Conversion in biomass
There is vital meaning.
It is glucose, Portugal that glucide in biomass, which is converted into 5- ethoxyl methyl furfural to relate generally to polysaccharide hydrolysis,
Grape sugar is converted into 5 hydroxymethyl furfural, 5 hydroxymethyl furfural and ethyl alcohol by dehydration and dehydration generation 5- ethoxyl methyl occurs
Three processes of furfural.Glucose is converted to 5 hydroxymethyl furfural again and includes glucose isomerase and is converted into 5- at fructose and fructose dehydration
The concatenated reaction mechanism mechanism of reaction of two step of hydroxymethylfurfural.Extensive research is expanded both at home and abroad for these reactions, but still is faced with anti-
The problems such as answering low efficiency and being easy to produce environmental pollution,
Converting 5 hydroxymethyl furfural for glucide green high-efficient is all huge challenge all the time.Fructose, glucose, fibre
The cost of dimension element and lignocellulose-like biomass successively reduces, but is converted into the difficulty of 5 hydroxymethyl furfural and significantly rises
It is high.It attempts in spite of some researchs directly using cellulose and lignocellulose-like biomass as waste 5 hydroxymethyl furfural,
But only chromic salts can obtain higher 5 hydroxymethyl furfural yield, direct conversion of biomass still suffer from severe reaction conditions,
Low efficiency, pollution weight and catalyst are difficult to the problem of recycling.Limitation biomass produces the key of 5 hydroxymethyl furfural, mainly
Be glucose be converted into 5 hydroxymethyl furfural efficiency and selectivity it is lower.
5 hydroxymethyl furfural can occur etherification reaction with ethyl alcohol and generate 5- ethoxyl methyl furfural.5 hydroxymethyl furfural with
Ethanol synthesis can also generate the by-products such as ethyl levulinate and acetal while generating 5- ethoxyl methyl furfural.Due to lacking
It is weary by glucose isomerase at the ability of fructose, the efficiency that glucose is converted to 5- ethoxyl methyl furfural by bronsted acid is very
Low, weak lewis acidity catalyst major catalytic side reaction, and strong lewis acid can select 5 hydroxymethyl furfural and ethyl alcohol
Selecting property it is converted into 5- ethoxyl methyl furfural.The catalyst of glucose isomerase is added in reaction system, is helped to realize
It is converted from glucose to a step of 5- ethoxyl methyl furfural.
Patent (CN201110223487.6) discloses a kind of heteropoly acid catalysis ethyl alcohol and 5- using Keggin-type structure
Hydroxymethylfurfural reacts the method for preparing 5- ethoxyl methyl furfural, and yield is up to 76% or more.Patent (application number:
CN201810543431.0 it) discloses a kind of using trifluoromethanesulfonic acid aluminium and ion exchange resin Amberlyst-15 as catalysis
Agent, the method that 5- ethoxymethyl furfural is converted glucose into the total solution system that dehydrated alcohol and dimethyl sulfoxide form,
The highest yield of 5- ethoxymethyl furfural is up to 48.8% under the conditions of 140~160 DEG C.Patent (application number:
CN201810485399.5 it) discloses a kind of using USY molecular sieve as solid catalyst, is formed in ethyl alcohol and tetrahydrofuran
The method that biomass straw is converted 5- ethoxymethyl furfural by the mixed solvent, 5- ethoxymethyl furaldehyde yield highest can reach
To 33%.Patent (application number: CN201510770684.8) is disclosed a kind of be used as using CT-700 and Amberlyst-15 and urged
Agent, the method for Microwave-assisted synthesis 5- ethoxymethyl furfural.Patent (application number: CN201510770684.8) discloses one
Kind, as catalyst, utilizes microwave-assisted glucide and ethanol synthesis to synthesize 5- ethoxy using CT-700 and Amberlyst-15
The method of methyl furfural.
However, being needed in above-mentioned technology simultaneously using lewis acid and bronsted acid as the catalyst to being catalyzed respectively de-
Water reaction and etherification reaction.Levulic acid and formic acid, 5- hydroxyl are decomposed into since bronsted acid can also be catalyzed 5 hydroxymethyl furfural
Methyl furfural and reaction intermediate are condensed into the side reactions such as humin, lead to the reaction efficiency reduction of entire conversion process and 5- second
Oxygen methyl furfural is selectively lower, to reduce the green and economy of entire conversion process, limits practical application.
Summary of the invention
The traditional technology side reaction for being converted into 5- alkoxymethylfurfural present invention aim to address glucide is more, imitates
Rate is low and the low problem of selectivity, converts glucide to providing a kind of green high-efficient the side of 5- alkoxymethylfurfural
Method, it is characterised in that the following steps are included:
Using the ionic liquid for containing bromide ion or the eutectic solvent for containing bromide ion as reaction phase, made using organic solvent
To extract phase, reaction is mutually mutually mixed to form two-phase system according to the mass ratio of 1:10 ~ 20:1 with extraction, is turned as glucide
The reaction medium of change；
By with strong lewis acid solid acid catalyst, glucide raw material, alcohols material raw material, reaction medium is according to one
Determine mass ratio to be added in reactor, under certain reaction temperature and stirring condition, the solid acid with strong lewis acid
Catalyst can not only be catalyzed the isomerization reaction of glucide, moreover it is possible to which the etherificate for being catalyzed 5 hydroxymethyl furfural and alcohols material is anti-
It answers, and the ionic liquid containing bromide ion or the eutectic solvent containing bromide ion can be with catalytic and dehydration reactions, so as to incite somebody to action
Glucide raw material continuously converts 5- alkoxymethylfurfural.
The method for preparing 5- alkoxymethylfurfural using glucide, wherein glucide raw material includes: fruit
Sugar, glucose, mannose, maltose, cellobiose and inulin, starch, hemicellulose, cellulose, lignocellulosic or
The hydrolyzate of lignocellulose-like biomass and kitchen garbage.
The method for preparing 5- alkoxymethylfurfural using glucide, wherein alcohols material raw material includes first
Alcohol, ethyl alcohol, normal propyl alcohol, isopropanol, n-butanol, ethylene glycol, glycerol etc..
The method for preparing 5- alkoxymethylfurfural using glucide, wherein reaction mutually includes: that bromide ion is made
The ionic liquid constituted respectively with imidazoles, pyridines, pyrroles's cationoid for anion；Choline bromide as hydrogen bond receptor with
Urea, thiocarbamide, phenylacetic acid, malic acid, citric acid, succinic acid, ethylene glycol, glycerol, butanediol, xylitol, amino acid, grape
The eutectic solvent that sugar, fructose, trifluoroacetamide are constructed as hydrogen bond donor.
The method for preparing 5- alkoxymethylfurfural using glucide, wherein organic solvent includes benzene, first
Benzene, dimethylbenzene, pentane, hexane, octane, hexamethylene, cyclohexanone, toluene cyclohexanone, chlorobenzene, dichloro-benzenes, methylene chloride, ether,
Propylene oxide, methyl acetate, ethyl acetate, propyl acetate etc., acetone, espeleton, methylisobutylketone, methyl isopropyl Ketone,
Glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, butyl cellosolve, glycol dimethyl ether, gamma-valerolactone, 2,
5- dimethyl furan, methylfuran, acetonitrile, pyridine, phenol, gasoline, diesel oil, kerosene, naphtha, ethanol petrol or petroleum ether.
The method for preparing 5- alkoxymethylfurfural using glucide, wherein with strong lewis acid
Solid acid catalyst includes metal oxide；Metal phosphate；And load magnesium ion, aluminium ion, calcium ion, scandium ion, titanium
Ion, chromium ion, iron ion, copper ion, gallium ion, germanium ion, ruthenium ion, zirconium ion, niobium ion, molybdenum ion, indium ion, tin
The metal oxidation of ion, lanthanum ion, cerium ion, ytterbium ion, hafnium ion, tantalum ion, tungsten ion, rhenium ion, iridium ion, platinum ion
Object and metal phosphate.
The method for preparing 5- alkoxymethylfurfural using glucide, wherein reaction temperature is 0-280 DEG C,
Stirring rate turns for 0-6000.
Preferably, the glucide raw material includes: fructose, glucose, mannose, maltose, cellobiose.
Preferably, with strong lewis acid solid acid catalyst mainly include load aluminium ion, titanium ion, tin from
Son, tungsten ion, niobium ion, hafnium ion, tantalum ion metal oxide and metal phosphate.
Preferably, the metal oxide and metal phosphate include magnesia, aluminium oxide, calcium oxide, iron oxide, oxygen
Change copper, zirconium oxide, niobium oxide, molybdenum oxide, tungsten oxide, tin oxide, cerium oxide, tantalum oxide, hafnium oxide, magnesium phosphate, aluminum phosphate, phosphorus
Sour calcium, ferric phosphate, cupric phosphate, basic zirconium phosphate, niobium phosphate, phosphoric acid tin, cerous phosphate, phosphoric acid tantalum, phosphoric acid hafnium.
It is further preferred that the metal oxide and metal phosphate includes aluminium oxide, calcium oxide, zirconium oxide, oxygen
Change niobium, molybdenum oxide, tungsten oxide, cerium oxide, aluminum phosphate, calcium phosphate, niobium phosphate, phosphoric acid tin, phosphoric acid tantalum, phosphoric acid hafnium.
Preferably, the organic solvent include butyl cellosolve, glycol dimethyl ether, gamma-valerolactone, gasoline, diesel oil,
Kerosene, naphtha, ethanol petrol or petroleum ether.
Preferably, the reaction temperature is 70-160 DEG C, and the stirring rate turns for 800-1600.
The advantages of the present invention are: being converted into 5- alkoxy first using glucide the present invention provides a kind of
The method of base furfural, the present invention is using the solid acid catalyst with strong lewis acid and has catalytic dehydration active brominated
The ionic liquid of ion or the eutectic solvent of bromine ion-containing construct catalyst system, and substitution contains lewis acid and Bu Langsi simultaneously
The conventional catalyst system of special acid, can reduce the side reaction of bronsted acid catalysis, greatly improve reaction efficiency and selectivity, mention
High-carbohydrate substance is converted into transformation efficiency, green and the economy of 5- alkoxymethylfurfural class A fuel A additive, using liquid
State fuel as extract mutually can reduce it is subsequent isolate and purify process, directly by 5- alkoxymethylfurfural class A fuel A additive
It is integrated into liquid fuel product.
Specific embodiment
The present invention is described in further detail by following embodiment, but the technology contents that are described of the present embodiment be it is illustrative,
Without being restrictive, protection scope of the present invention should not be limited to according to this.
Embodiment 1
0.1 gram of glucose is added in 15 mL reactors, 1 g ionic liquid 1- ethyl-3-methylimidazole bromide is separately added into
Water and 2 mL ethyl alcohol add 2 mL gasoline, and 0.2 g phosphoric acid tin catalyst is added.Being kept stirring speed is 700 revs/min,
It is reacted 6 hours under the conditions of 140 DEG C, separates organic phase, 5- ethoxyl methyl furaldehyde yield is 80% in organic phase.
Embodiment 2
0.1 gram of cellulosic hydrolysate is added in 15 mL reactors, 1 g ionic liquid 1- ethyl -3- methyl miaow is separately added into
Azoles bromide water and 2 mL ethyl alcohol add 2 mL glycol dimethyl ethers, and 0.2g titanium dichloride load tin catalyst is added.It keeps
Mixing speed is 700 revs/min, is reacted 8 hours under the conditions of 160 DEG C, and organic phase, 5- ethoxyl methyl in organic phase are separated
Furfural is 65%.
Claims (11)
1. a kind of green high-efficient provided by the invention using glucide 5- alkoxymethylfurfural method, feature exists
In the following steps are included: using the ionic liquid for containing bromide ion or the eutectic solvent for containing bromide ion as reaction phase, benefit
It uses organic solvent as phase is extracted, reaction is mutually mutually mixed to form two-phase system according to the mass ratio of 1:10 ~ 20:1 with extraction, is made
For the reaction medium of glucide conversion；By solid acid catalyst, glucide raw material, alcohols object with strong lewis acid
Matter raw material, reaction medium are added in reactor according to certain mass ratio, by glucide raw material under the conditions of heating and stirring
Continuous conversion 5- alkoxymethylfurfural.
2. the method according to claim 1 for preparing 5- alkoxymethylfurfural using glucide, wherein glucide
Raw material includes: fructose, glucose, mannose, maltose, cellobiose and inulin, starch, hemicellulose, cellulose, wood
The hydrolyzate of matter cellulose or lignocellulose-like biomass and kitchen garbage.
3. the method according to claim 1 for preparing 5- alkoxymethylfurfural using glucide, wherein alcohols material
Raw material includes methanol, ethyl alcohol, normal propyl alcohol, isopropanol, n-butanol, ethylene glycol, glycerol etc..
4. the method for preparing 5- alkoxymethylfurfural using glucide according to claim 1, wherein anti-
It should mutually include: the ionic liquid that bromide ion is constituted with cations such as imidazoles, pyridines, pyroles respectively as anion；Bromine
Change choline as hydrogen bond receptor and urea, thiocarbamide, phenylacetic acid, malic acid, citric acid, succinic acid, ethylene glycol, glycerol, butanediol,
The eutectic solvent that xylitol, amino acid, glucose, fructose, trifluoroacetamide are constructed as hydrogen bond donor.
5. the method according to claim 1 for preparing liquid fuel using biomass, wherein organic solvent include fragrant benzene,
Toluene, dimethylbenzene, pentane, hexane, octane, hexamethylene, cyclohexanone, toluene cyclohexanone, chlorobenzene, dichloro-benzenes, methylene chloride, second
Ether, propylene oxide, methyl acetate, ethyl acetate, propyl acetate etc., acetone, espeleton, methylisobutylketone, isopropyl methyl
Ketone, glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, butyl cellosolve, glycol dimethyl ether, in γ-penta
Ester, 2,5- dimethyl furan, methylfuran, acetonitrile, pyridine, phenol, gasoline, diesel oil, kerosene, naphtha, ethanol petrol or stone
Oily ether.
6. the method according to claim 1 for preparing liquid fuel using biomass, wherein with strong lewis acid
Solid acid catalyst includes metal oxide；Metal phosphate；And load magnesium ion, aluminium ion, calcium ion, scandium ion, titanium
Ion, chromium ion, iron ion, copper ion, gallium ion, germanium ion, ruthenium ion, zirconium ion, niobium ion, molybdenum ion, indium ion, tin
The metal oxidation of ion, lanthanum ion, cerium ion, ytterbium ion, hafnium ion, tantalum ion, tungsten ion, rhenium ion, iridium ion, platinum ion
Object and metal phosphate.
7. the method according to claim 1 for preparing liquid fuel using biomass, wherein glucide raw material includes:
Fructose, glucose, mannose, maltose, cellobiose.
8. the method according to claim 1 for preparing liquid fuel using biomass, wherein with strong lewis acid
Solid acid catalyst includes the metal oxygen for loading aluminium ion, titanium ion, tin ion, tungsten ion, niobium ion, hafnium ion, tantalum ion
Compound or metal phosphate.
9. the method according to claim 1 for preparing liquid fuel using biomass, the metal oxide and metal
Phosphate includes magnesia, aluminium oxide, calcium oxide, iron oxide, copper oxide, zirconium oxide, niobium oxide, molybdenum oxide, tungsten oxide, oxidation
Tin, cerium oxide, tantalum oxide, hafnium oxide, magnesium phosphate, aluminum phosphate, calcium phosphate, ferric phosphate, cupric phosphate, basic zirconium phosphate, niobium phosphate, phosphoric acid
Tin, cerous phosphate, phosphoric acid tantalum, phosphoric acid hafnium.
10. the method according to claim 1 for preparing liquid fuel using biomass, the metal oxide and metal
Phosphate includes aluminium oxide, calcium oxide, zirconium oxide, niobium oxide, molybdenum oxide, tungsten oxide, cerium oxide, aluminum phosphate, calcium phosphate, phosphoric acid
Niobium, phosphoric acid tin, phosphoric acid tantalum, phosphoric acid hafnium.
11. the method according to claim 1 for preparing liquid fuel using biomass, the organic solvent include ethylene glycol
Butyl oxide, glycol dimethyl ether, gamma-valerolactone, gasoline, diesel oil, kerosene, naphtha, ethanol petrol or petroleum ether.
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| CN111057594A (en) * | 2019-12-30 | 2020-04-24 | 李旭 | Preparation method of alcohol-based fuel additive |
| CN112321546A (en) * | 2020-11-06 | 2021-02-05 | 南开大学 | Method for converting hemicellulose into acetal and furfural in low-boiling-point solvent |
| CN112608289A (en) * | 2020-12-21 | 2021-04-06 | 中国科学院广州能源研究所 | Method for efficiently preparing 5-hydroxymethylfurfural by catalyzing bio-based fructose through organic solvent-ionic liquid composite system |
| CN114456133A (en) * | 2022-01-27 | 2022-05-10 | 南开大学 | Method for preparing 5-ethoxymethylfurfural by catalyzing fructose through sulfonated zirconium phosphate |
| CN114736129A (en) * | 2022-04-06 | 2022-07-12 | 中国科学院成都有机化学有限公司 | Dicarboxylic acid-based eutectic solvent and preparation method and application thereof |
| CN115138392A (en) * | 2022-09-05 | 2022-10-04 | 农业农村部环境保护科研监测所 | Multifunctional biochar catalyst rich in oxygen-containing functional groups and preparation method thereof |
| CN115304565A (en) * | 2022-02-22 | 2022-11-08 | 南开大学 | Method for preparing 5-ethoxymethylfurfural by using porous carbon-based solid acid catalysis |
| CN116178316A (en) * | 2021-11-29 | 2023-05-30 | 中国科学院宁波材料技术与工程研究所 | Method for preparing 5-hydroxymethyl-2-furaldehyde by using fructose |
| CN116270254A (en) * | 2022-11-28 | 2023-06-23 | 昆明理工大学 | Preparation method and application of amorphous calcium phosphate-cerium phosphate composite material |
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| CN111057594A (en) * | 2019-12-30 | 2020-04-24 | 李旭 | Preparation method of alcohol-based fuel additive |
| CN112321546A (en) * | 2020-11-06 | 2021-02-05 | 南开大学 | Method for converting hemicellulose into acetal and furfural in low-boiling-point solvent |
| CN112608289A (en) * | 2020-12-21 | 2021-04-06 | 中国科学院广州能源研究所 | Method for efficiently preparing 5-hydroxymethylfurfural by catalyzing bio-based fructose through organic solvent-ionic liquid composite system |
| CN112608289B (en) * | 2020-12-21 | 2023-09-05 | 中国科学院广州能源研究所 | Method for efficiently preparing 5-hydroxymethylfurfural by catalyzing bio-based fructose through organic solvent-ionic liquid composite system |
| CN116178316A (en) * | 2021-11-29 | 2023-05-30 | 中国科学院宁波材料技术与工程研究所 | Method for preparing 5-hydroxymethyl-2-furaldehyde by using fructose |
| CN114456133A (en) * | 2022-01-27 | 2022-05-10 | 南开大学 | Method for preparing 5-ethoxymethylfurfural by catalyzing fructose through sulfonated zirconium phosphate |
| CN114456133B (en) * | 2022-01-27 | 2022-12-30 | 南开大学 | Method for preparing 5-ethoxymethylfurfural by catalyzing fructose through sulfonated zirconium phosphate |
| CN115304565A (en) * | 2022-02-22 | 2022-11-08 | 南开大学 | Method for preparing 5-ethoxymethylfurfural by using porous carbon-based solid acid catalysis |
| CN114736129A (en) * | 2022-04-06 | 2022-07-12 | 中国科学院成都有机化学有限公司 | Dicarboxylic acid-based eutectic solvent and preparation method and application thereof |
| CN115138392A (en) * | 2022-09-05 | 2022-10-04 | 农业农村部环境保护科研监测所 | Multifunctional biochar catalyst rich in oxygen-containing functional groups and preparation method thereof |
| CN116270254A (en) * | 2022-11-28 | 2023-06-23 | 昆明理工大学 | Preparation method and application of amorphous calcium phosphate-cerium phosphate composite material |
| CN116270254B (en) * | 2022-11-28 | 2024-03-19 | 昆明理工大学 | Preparation method and application of amorphous calcium phosphate-cerium phosphate composite material |
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Address after: 300071 Tianjin City, Nankai District Wei Jin Road No. 94 Applicant after: NANKAI University Applicant after: Tianjin Pickup Selling Technology Group Co.,Ltd. Address before: 300071 Tianjin City, Nankai District Wei Jin Road No. 94 Applicant before: NANKAI University Applicant before: TIANJIN CITY MINE TECHNOLOGY Co.,Ltd. |
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| CB02 | Change of applicant information |